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Grignard addition: phenylmagnesium bromide + benzaldehyde → diphenylmethanol
PhMgBr + Ph–CHO → [Ph2CH–OMgBr] →(H3O+) Ph2CH–OH
Textbook Grignard addition. Phenylmagnesium bromide (PhMgBr) attacks benzaldehyde's carbonyl carbon; aqueous acidic workup releases diphenylmethanol (benzhydrol). PhMgBr is bought as a 1 M or 3 M solution in anhydrous Et2O or THF — solid Grignards are not weighed. Reaction is run under N2 with rigorous water exclusion.
Conditions: Cool a flame-dried, N2-flushed flask to 0 °C. Charge anhydrous Et2O (~3 mL per mmol of benzaldehyde). Add benzaldehyde (1.0 equiv) by syringe; stir 5 min. Add PhMgBr (1.1 equiv, 1 M or 3 M solution in Et2O) dropwise over 10 min — exotherm; control addition rate to keep T < 5 °C. Warm to RT, stir 1–2 h. Workup — Quench cautiously with sat. NH4Cl (or 10 % HCl); extract with Et2O; wash organic with sat. NaHCO3 + brine; dry MgSO4. Concentrate. Recrystallise from hexane or hexane/EtOAc. White crystals; mp 65–67 °C.
- Expected yield
- 75–92 %
- Expected duration
- 1–2 h at RT after 0 °C addition
Computed quantities
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- FORMYL TRANSFER TO GRIGNARD REAGENTS WITH N-FORMYLPIPERIDINE: 3-PHENYLPROPIONALDEHYDE Organometallic addition
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